N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide | 1308878-46-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide
• 英文别名: 7,18-Bis[4-bromo-2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone；7,18-bis[4-bromo-2,6-di(propan-2-yl)phenyl]-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaene-6,8,17,19-tetrone
• CAS: 1308878-46-7
• 化学式: C₄₈H₄₀Br₂N₂O₄
• 分子量: 868.665
• InChiKey: NNZHNRYCLMMLSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.7
• 重原子数：
  56
• 可旋转键数：
  6
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  74.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide 、 4-甲酰基苯硼酸 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 24.0h， 以62%的产率得到4-[4-[18-[4-(4-Formylphenyl)-2,6-di(propan-2-yl)phenyl]-6,8,17,19-tetraoxo-7,18-diazaheptacyclo[14.6.2.22,5.03,12.04,9.013,23.020,24]hexacosa-1(23),2,4,9,11,13,15,20(24),21,25-decaen-7-yl]-3,5-di(propan-2-yl)phenyl]benzaldehyde
  参考文献：
  名称：

  Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye with Latent Bromo Groups for C–C Cross Coupling

  摘要：

  To address the absence of synthetic routes to access easily functionalizable, non-aggregating, and soluble bay-unsubstituted perylene bisimide dyes, an efficient, three-step, multigram-scale synthesis of the divergent building block N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide is reported. Suzuki coupling yields new dyes that maintain excellent solubility and exhibit unity quantum yields in CHCl3, THF, toluene, and CH3CN. The methodology reported here enables access to dyes with sensitive functional groups such as aldehydes that are not accessible by traditional imidization routes.

  DOI：

  10.1021/ol401946g
• 作为产物：
  描述：

  N,N’-bis(4-bromo-2,6-diisopropyl)-4,4’-binaphthyl-1,1’,8,8’-teracarboxylic bisimide 在 potassium carbonate 、 C.I.酸性橙108 作用下， 生成 N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide
  参考文献：
  名称：

  合成的由–和Per二酰亚胺组成的受体-供体-受体多发色团用于多步能量转移研究

  摘要：

  基于2010年在包含三甲苯二酰亚胺（TDI）和per二酰亚胺（PDI）的线性多发色团中单重态-单态an灭研究的结果，我们报告了成功合成TDI-PDI-TDI二聚体的详细过程。描述了无效的合成途径，这对于理解复杂的多色团的逐步构建是必需的，从而导致了通用的合成计划，涉及包含由刚性低聚亚苯基间隔基分隔的二甲苯二酰亚胺的多组分系统。

  DOI：

  10.1021/acs.chemmater.5b04602

文献信息

• Subcomponent Self-Assembly of a 4 nm M₄L₆Tetrahedron with Zn^IIVertices and Perylene Bisimide Dye Edges
  作者：Peter D. Frischmann、Valentin Kunz、Vladimir Stepanenko、Frank Würthner

  DOI：10.1002/chem.201405866

  日期：2015.2.9

  Formation of a tetrahedron with >4 nm perylene bisimide (PBI) dye edges and ZnII vertices in a one‐pot 22 component self‐assembly reaction is reported. The luminescent polyhedron equilibrates to a Zn2L3 helicate and disassembles upon dilution. Insights into the subcomponent self‐assembly of extended PBI ligands help to refine design rules for constructing large photofunctional metallosupramolecular hosts

  据报道，在一个单锅22组分自组装反应中，形成了具有> 4 nm的bi双酰亚胺（PBI）染料边缘和Zn II顶点的四面体。发光多面体平衡为Zn 2 L 3螺旋状，并在稀释后分解。深入了解扩展的PBI配体的子组件自组装有助于完善用于构建大型光功能性金属超分子主体的设计规则。
• Bright Fluorescence and Host-Guest Sensing with a Nanoscale M₄L₆Tetrahedron Accessed by Self-Assembly of Zinc-Imine Chelate Vertices and Perylene Bisimide Edges
  作者：Peter D. Frischmann、Valentin Kunz、Frank Würthner

  DOI：10.1002/anie.201501670

  日期：2015.6.15

  commonly utilized in subcomponent self‐assembly with ZnII and tris(2‐aminoethyl)amine provides access to a metallosupramolecular host with the rare combination of structural integrity at concentrations <10−7 mol L−1 and an exceptionally high fluorescence quantum yield of Φem=0.67. Encapsulation of multiple perylene or coronene guest molecules is accompanied by strong luminescence quenching. We anticipate

  据报道，高发光的Zn 4 L 6四面体具有3.8 nm的bi双酰亚胺边缘和六齿的Zn II-亚胺螯合顶点。用Zn II和三（2-氨基乙基）胺代替亚组分自组装中常用的Fe II和一元胺，可以获得金属超分子基质，其浓度小于10 -7  mol L -1且具有极高的结构完整性的罕见组合的荧光量子产率Φ EM= 0.67。多个per或co苯客体分子的封装伴随着强烈的发光猝灭。我们预计，这种自组装策略可能会得到推广，以改善对宿主-客体的光捕获，光催化和感测量身定制的明亮荧光配位笼的使用。
• Synthesis of an Acceptor–Donor–Acceptor Multichromophore Consisting of Terrylene and Perylene Diimides for Multistep Energy Transfer Studies
  作者：Sebastian Stappert、Chen Li、Klaus Müllen、Thomas Basché

  DOI：10.1021/acs.chemmater.5b04602

  日期：2016.2.9

  Motivated by the results obtained from the investigation of singlet–singlet annihilation in a linear multichromophore comprising terrylene diimides (TDI) and perylene diimide (PDI) in 2010, we report the detailed process toward the successful synthesis of a TDI–PDI–TDI dyad. Ineffective synthetic pathways, which were necessary for the understanding of the step-by-step construction of the complex multichromophore

  基于2010年在包含三甲苯二酰亚胺（TDI）和per二酰亚胺（PDI）的线性多发色团中单重态-单态an灭研究的结果，我们报告了成功合成TDI-PDI-TDI二聚体的详细过程。描述了无效的合成途径，这对于理解复杂的多色团的逐步构建是必需的，从而导致了通用的合成计划，涉及包含由刚性低聚亚苯基间隔基分隔的二甲苯二酰亚胺的多组分系统。
• Synthesis of a Non-aggregating Bay-Unsubstituted Perylene Bisimide Dye with Latent Bromo Groups for C–C Cross Coupling
  作者：Peter D. Frischmann、Frank Würthner

  DOI：10.1021/ol401946g

  日期：2013.9.20

  To address the absence of synthetic routes to access easily functionalizable, non-aggregating, and soluble bay-unsubstituted perylene bisimide dyes, an efficient, three-step, multigram-scale synthesis of the divergent building block N,N'-bis(4-bromo-2,6-diisopropylphenyl)perylene-3,4:9,10-tetracarboxylic bisimide is reported. Suzuki coupling yields new dyes that maintain excellent solubility and exhibit unity quantum yields in CHCl3, THF, toluene, and CH3CN. The methodology reported here enables access to dyes with sensitive functional groups such as aldehydes that are not accessible by traditional imidization routes.